Chicago’s Tech Leaders Share the Secrets of Keeping a Startup Afloat

August 22, 2016

The startup culture has laid its existence on pretty thick the past few years, yet it’s still regarded as sexy because of its consistent pursuit to be better. The joke on the West Coast is, “If you aren’t working at a startup, you can’t get a date on Friday night.”

The startup world can seem extremely attractive from the outside, but what is often overlooked is the reality of a startup, especially one in its early stages. The solution isn’t obvious and success isn’t guaranteed.

”You have to be a little insane to work at a startup,” Rick Zullo, vice president at Lightbank, says.

“You have to be a little bit crazy to start a company. It can be one of the most fulfilling things in the world, but you need to have an irrational love for working with really talented and ambitious people who are building products that impact people’s lives. That’s the beauty of technology.”

Last Thursday, TechNexus held a technology panel for tech fanatics, startup owners and the like to discuss and dissect circulating issues that young tech businesses face today. These issue include improving efficiency, predicting failures, finding safety and security problems and more.

The point of the event was for tech leaders to share the technically complex challenges regarding what it takes to start a company from the ground up, and surprisingly, what kind of person it takes to actually be successful in the startup world that everyone seems to be so intrigued by.

The panel, sponsored by MeetUp Chicago, featured influential tech executives from the Chicago area, including:

They all share their frustrations and successes as technology startups, coming together to try and find solutions to the common problems attached to behind-the-scene technology and everything that comes along with it, which is a lot.

The panel. Photo by author.

These hard-core technologists are looking for opportunities to collaborate with other influential leaders in the tech realm. They are on their way to building a more elaborate community on the enterprise side of technology in Chicago, finding creative ways for leaders, executives and founders to build a stronger tech community.

Recruiting Process

The panel kicked off targeting the main issues the Chicago technology community faces today, with the resounding challenge revolving around the traditional process of hiring; perhaps the greatest challenge for any startup.

Finding people you can trust to utilize the front lines of your business is an incredibly difficult and somewhat sensitive feat, often ending in a constant search for the perfect candidate.

Breaking the traditional style of recruiting, many tech leaders have found the most reliable way of finding good matches for their companies is through attending networking events in the city, where like-minded and ambitious individuals are bound to be.

Carranza is a big advocate for this recruiting tactic, leveraging her network (everyone she has interacted with over the last 10 years, plus social media outreach and of course, MeetUps) to identify high performers who are passionate about the work they do, have an interest in security and are willing to learn.

Carranza explains it simply, saying “As opposed to, ‘This is the type of person we are looking for, and these are the specific skill sets that we need,’ we focus the conversation around ‘This is what we need you to accomplish. Do you think you can do it?'”

If the answer is yes, Carranza has applicants explain to her what they have done in the past that deems them suitable for the position, and what kind of transferable skills they can leverage to be successful for the available opportunity. She claimed this process has been very successful so far.

Each tech executive was in compliance with the greatest challenge concerning technology also being the greatest adventure, explaining that some challenges are unique to Chicago — and some are not — but what it really comes down to are the people.

”We are working with innovative, young companies that are coming up with awesome ideas, while staying up to pace with the demands of the market and the consumer,” Rocio Baeza from Jemurai says.

“While fresh faces, new ideas and new energy is incredibly motivating, it is also extremely challenging because we are all starting from scratch, looking at successful businesses that have made it and learning from them.”

What’s Helping Propel the Chicago Tech Community?

Something that is different from other ecosystems that is extremely dense here in Chicago are development boot camps. Rather than rely on a Perdue graduate’s resume, more and more employers are turning to modern methods of finding the best talent, with boot camps at the forefront of the search.

In comparison to the previously trusted four-year education route, being part of a boot camp program shows recruiters a different level of seriousness and initiative that’s missing in the workforce today.

Jimoh from Opternative thinks boot camps are an amazing force in transforming individuals into tech experts, leading to the building of better technology teams for startups.

“We love them,” Jimoh says. “Someone who is attending a boot camp is someone who is making the decision to seek out what they want on their own, creating an environment that is similar to startups. There is a mix of people who are self-taught, some from the traditional background of a four-year university and some experienced folks that have worked in other startups.”

Schwarz from BenchPrep agrees with Jimoh.

”Everything comes down to the people,” Schwarz states. “Boot camps are a great clean slate because they are filled with people who are eager to learn something new because they just switched careers, or they are continuing to pick up things they didn’t get elsewhere.”

People Looking to Join the Startup World

Like any type of job, working for a startup has its perks and its downfalls. It isn’t just about being your own boss and being able to wear shorts to work.

It takes a certain type of person to dedicate the kind of time and energy it takes to keep an early business running and growing. It isn’t just ping pong and parties and kegerators. And when you give people the reality of it, it opens their eyes.

Jimoh was serious and passionate on this subject, hitting home with people claiming they want to work for a startup or start their own company needing to ask themselves, “Do you want to work for a company that has no process yet, no HR department, no benefits and work longer hours?”

He continues, saying, “I wanted to create something out of nothing. I wanted to create something new. It was about wanting to solve new and challenging problems, not being in a routine lifestyle of clocking in and clocking out.”

Carranza followed up by saying that talent is so rare, yet compliance issues are so real, telling event attendees the tech startup field is not for you unless you have an inquisitive mind, you like challenges and you are incredibly curious.

“You blink the wrong way or you leave the wrong door open…the littlest thing can be devastating to your application and your company,” she explains.

“You can’t walk into developing any application that’s going to be used by the public and just phone it in. You’ve got to do the work. It’s the most boring, technical, sometimes mind-numbing, head-scratching process, and you’ve got to go through it from the ground up.”

Looking Forward to the Future of Chicago

Closing on how to make Chicago a better tech city, all six executives were in unison on the “coming together” notion of making that happen. Being able to share and interact with other tech companies is so essential because developers, coders or whoever it may be, get so deep into what they are building that they are no longer learning from the other tech companies out there.

Rocio Baeza takes it a step further, incorporating political issues.

“If we’re able to create a more diverse technical community, and I’m talking about gender, race and background, I think that will create an environment where we can learn from each other. If we open that up and front things as a way to solve a specific problem, I think we can do even more amazing things in the tech space.”

If you have an idea and think you can create something out of nothing, know going into it that that requires an enormous amount of discipline, financial backing and support from those around you.

With the accessibility of technology, we are part of an age where anybody can do that, but having the tenacity to keep it running is the ultimate challenge.